The Keys · Key Largo
Baker's Cay, the resort on the bayside of Key Largo, keeps 14-foot Hobie Waves on its beach through Scuppers, by the hour, briefing and life vest included, beginners welcome. As of October 2026 the Hobie is booked by phone, not online. A second base is on St. Pete Beach.
Featured Daysail The Keys · Marathon
Sirius is a Coast Guard inspected 36-foot sailing catamaran carrying 24 guests from Safe Harbor Marathon Marina, running two-hour sunset cruises by the seat and private charters. Capt. Dale Kamerzel has run the company since 2000. Siriusly Nauti is a motor boat.
Featured Daysail The Keys · Key West
Crewed daysails on Hindu, a 1925 gaff-rigged schooner designed by William H. Hand Jr. as a half-scale Grand Banks fisherman, later a WWII Navy patrol boat and Provincetown whale-watcher. Winter sunset and daytime sails out of the Historic Seaport.
Daysail The Keys · Key West
Year-round crewed sails on a 75-foot Key West-built catamaran from Sunset Pier at the foot of Duval Street. Nightly sunset cruises, Sunday brunch sails October to May and a Sunday swim-and-lunch sail in summer, private charters, food and drink in every fare.